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Condo holiday rentals in Siena

Find and book unique condos on Airbnb

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Popular amenities for Siena condo rentals

Weekly condo rentals

Top Guest favourite
Condo in Strada In Chianti
4.95 out of 5 average rating, 370 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

DrewRating, 5 stars5 days ago
I highly recommend Bryan's place it is extremely beautiful and well maintained with an amazing back drop. Bryan and his family are very welcoming. If you want a taste of Tuscany you need to stay here.
Top Guest favourite
Condo in San Niccolò
4.99 out of 5 average rating, 250 reviews

The View of Sangiorgio

MatthewRating, 5 stars3 days ago
This is the second time I have stayed at this Airbnb. Mattia is a consummate host. He responds quickly and is always pleasant. The apartment and especially the terrace are phenomenal. I hate to give it such high marks because everybody is gonna wanna steal it from me! But it is a well-deserved high recommendation.I really love this place and it feels like my second home.
Top Guest favourite
Condo in Greve in Chianti
4.98 out of 5 average rating, 160 reviews

The Nest in Chianti

LesRating, 5 stars6 days ago
Brilliant Airbnb in Greve.. location superb overlooking the square. The apartment is spacious and felt like home. Wonderful restaurants to walk to and a great bakery opposite for morning coffee and pastries. Easy to park the car just a few minutes walk away. Lovely villages to explore nearby and picture perfect everywhere you look. If you come to Greve book here, relax and soak up the Italian atmosphere. Cora is a fantastic host who regularly communicates to make sure you have everything you need. 10/10 ❤️
Top Guest favourite
Condo in Lucca
5 out of 5 average rating, 233 reviews

Taste of Lucca, charming and modern apartment

RobinRating, 5 stars3 weeks ago
The apartment is gorgeous inside. The kitchen was very well stocked, and quite modern. We had a little trouble finding it, but we are unfamiliar with Lucca. Lovely restaurants in all directions and cute shops. Leandro was a wonderful host . Peaceful and relaxing stay.
Top Guest favourite
Condo in Siena
4.86 out of 5 average rating, 348 reviews

Apartment in the heart of Siena

SharonRating, 5 stars5 days ago
Ideal location walkable from bus station. Parking is difficult in Siena, but there's free parking available in this area. Right on the edge of center. Very quiet. Near the fortress, a great place to walk or jog in the morning. We felt far away from the hustle and bustle but right in the heart of the city at the same time. Peaceful and comfortable. Nicely decorated. Enjoyed our stay. Aida is very friendly and helpful.
Top Guest favourite
Condo in Colle di Val d'Elsa
4.98 out of 5 average rating, 180 reviews

DorminColle - Tuscan-style apartment

NunoRating, 5 stars2 weeks ago
This place is great, I strongly recommend it. The hosts are also amazing. We stayed while doing a bike trip around Tuscany and the hosts allowed us to store our bikes in their garage.
Guest favourite
Condo in Montepulciano
4.92 out of 5 average rating, 124 reviews

"Dimora Valinda" Montepulciano Piazza Grande +A/C

StefanieRating, 5 stars5 days ago
We had the best time!! The cutest little apartment with a nice little balcony. Loved the exposed beams and the kitchen. It was very walkable to great restaurants and scenic views, also far enough away were you are not worried about noise at night. Host was super responsive and had excellent recommendations on where to eat and what to do!
Top Guest favourite
Condo in Monteriggioni
4.92 out of 5 average rating, 122 reviews

Il Vecchio Noce

JuliaRating, 5 stars2 weeks ago
A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise quite doable if you drive slowly. But it is also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. Somewhat annoying is the squeaky gas heater and the fact that the water temperature in the shower fluctuated quite a bit. Maybe it can still be repaired. But that's already whining at a high level. All in all, a great place to stay with a very nice and accommodating host.

Pet-friendly condo rentals

Guest favourite
Condo in Gambassi Terme
4.89 out of 5 average rating, 232 reviews

A View Over Tuscany's Countryside

OliverRating, 5 stars3 weeks ago
We spent 8 days in Filippo's apartment and explored Tuscany. Our goals were relatively centrally accessible. That's why we chose this place. Beautiful Tuscan-style apartment that leaves nothing to be desired. There is everything you need. We were also able to use the small cozy terrace in front of the entrance more often! The car is safe in the locked yard and there are also shopping facilities nearby. Upon our arrival, Filippo was personally present and gave us tips and explanations! Our conclusion: Very nice and reliable host and a great accommodation!
Guest favourite
Condo in Siena
4.76 out of 5 average rating, 111 reviews

Francesco's house

BrankaRating, 5 stars1 week ago
The apartment was great and met all my expectations! It was very clean and comfortable. The location is perfect — close to the city center and just a short walk from charming streets ideal for walking and exploring. The host provided all the information we needed, which made our stay smooth and easy. I would definitely recommend this place and would love to stay here again.
Guest favourite
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars3 weeks ago
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.
Guest favourite
Condo in Morrona
4.86 out of 5 average rating, 441 reviews

Stylish Terrace on Boboli Gardens

KellyRating, 5 stars6 days ago
We loved this space and when we come to Florence again we will most definitely book here. It was a cool, quiet oasis on the beautiful relaxing side of the Arno. The location was perfect with an easy walk to all the sites but also so quiet and peaceful. We loved the kitchen and cooked multiple days and sat on the sweet patio and enjoyed the local wine. The space was clean and cool and the layout was perfect for 2 people. There’s also a couch bed if another person or one or two children were there. Our hosts were so accommodating and friendly! We have so much love for this special spot in Florence.
Guest favourite
Condo in Florence
4.95 out of 5 average rating, 143 reviews

Designer Apartment with Breathtaking Views

ScottRating, 5 stars1 month ago
I enjoyed my stay at Dan's apartment. It was large (even more so when you factor in the adjacent terrace), beautifully furnished and well stocked. Appreciated the dishwasher and clothes washer. Having a second bathroom was an extra perk. Only slight downside was the walk into the center of town (25 min to the Ufizzi) as it rained nearly every day during my weeklong stay -- I imagine on dry/temperate days it's a pleasant walk along the river. Overall I would gladly stay again.
Guest favourite
Condo in San Gimignano
4.83 out of 5 average rating, 236 reviews

Historic centre - cozy apartment

ArcadiaRating, 5 stars1 week ago
We loved staying at Helga and Federico’s apartment! The place was very clean and nearby one of the main gates, with many restaurants, parking options, and things to do. Federico gave us recommendations for places to go, and it is clear he loves this town!
Top Guest favourite
Condo in Centro Storico
4.99 out of 5 average rating, 115 reviews

Asso's Place, Luxury Apartment with stunning view

PatrickRating, 5 stars1 month ago
Asso's Place was the perfect home for our family in Florence!  The most luxurious Air BnB we've found to date - with original paintings, a generous supply of records, DVDs, and books galore.  The Duomo felt so close that we could reach out the window and touch it. The location was walking distance from all the major attractions and excellent restaurants. Piero and Raffaela were perfect hosts, reaching out to us with information about restaurants, shopping, and sites to visit, and answering every question quickly. Raffaella greeted us in person and pointed out important features of the apartment.  All of our needs were met to perfection.
Guest favourite
Condo in Pienza
4.91 out of 5 average rating, 99 reviews

Amazing view of Val d'Orcia Pienza

AnneRating, 5 stars3 weeks ago
Very comfortable accommodations and gorgeous property and views

Condo rentals with a pool

Superhost
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment.

TomRating, 5 stars4 days ago
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.
Guest favourite
Condo in Monte San Savino
4.96 out of 5 average rating, 49 reviews

La Foresteria | Granary House

LynneRating, 5 stars2 weeks ago
Such a beautiful, peaceful place to spend a few days! It was central to many tours and activities, great for exploring! Luca was a wonderful host and ensured we were happy and had everything we needed. The restaurant was great! I can’t think of anything that would have made our stay better! Completely exceeded our expectations!
Superhost
Condo in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco – Bellavista – Castello di Bossi

GaiaRating, 5 stars9 months ago
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended
Guest favourite
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 470 reviews

Casa Rebecca with a small private pool

SophieRating, 5 stars2 weeks ago
Amazing place !! It really worth !
Guest favourite
Condo in Careggi
4.92 out of 5 average rating, 166 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars2 days ago
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.
Top Guest favourite
Condo in Castellina in Chianti
4.91 out of 5 average rating, 58 reviews

Apartment with terrace and stunning view

AlexRating, 5 stars1 week ago
The apartment was lovely. We stayed there for 6 days from end of May into start of June. The view is incredible and the fact there is a nice balcony and a swimming pool that look over it are a bonus. Raisa was very helpful with suggestions for the area, and they let us do our own thing on the land peacefully. The dogs are very adorable and friendly too! For anyone looking for a peaceful getaway with the occasional trip into Castelina in Chianti (would recommend there are many lovely spots to eat), this is a perfect getaway.
Guest favourite
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Castello di Orgiale Charme Residenz

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!
Guest favourite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 156 reviews

La Casetta

RamRating, 5 stars3 weeks ago
Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!

Quick stats about condo rentals in Siena

  • Total rentals

    240 properties

  • Nightly prices starting at

    $50 NZD before taxes and fees

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Condo rentals